The first Pd-catalyzed Buchwald-Hartwig aminations at C-2 or C-4 in the estrone series.

ABSTRACT: A facile Pd-catalyzed C(sp²)-N coupling to provide a range of 2- or 4-[(subst.)phenyl]amino-13α-estrone derivatives has been achieved under microwave irradiation. The reactions were mediated with the use of Pd(OAc)₂ as a catalyst and KOt-Bu as a base in the presence of X-Phos as a ligand. The desired products have been obtained in good to excellent yields. The nature and the position of the aniline substituent at the aromatic ring influenced the outcome of the couplings. 2-Amino-13α-estrone was also synthesized in a two-step protocol including an amination of 2-bromo-13α-estrone 3-benzyl ether with benzophenone imine and subsequent hydrogenolysis.

SUBMITTER: Bacsa I 

PROVIDER: S-EPMC6009172 | biostudies-literature | 2018

REPOSITORIES: biostudies-literature